title: Synthesis and antimicrobial properties of substituted 3-aminoxypropionyl and 3-aminoxy-(E)-2-methoxyiminopropionyl monobactams.
abstract: The substituted 3-aminoxyproprionyl (VII) and 3-aminoxy-(E)-2-methoxyiminopropionyl monobactams (VIII) which possess the monocyclic beta-lactam nucleus of aztreonam (IX) were synthesized by reaction of triethylammonium (3S, 4S)-3-amino-4-methyl-2-oxo-1-azetidinsulfonate with the aminoxy acids X and XI, respectively. Compounds VII and VIII were assayed in vitro for their antimicrobial properties against Gram-positive and Gram-negative bacteria, whether producers of beta-lactamases or otherwise. Both types of compounds (VII and VIII) exhibited a poor antibacterial activity towards Gram-positive bacteria, comparable to that of aztreonam. On the contrary VII and VIII proved to be practically inactive against Gram-negative microorganisms, towards which aztreonam exhibits a high degree of activity.
authors.affiliation: Istituto di Chimica Farmaceutica e Tossicologica, Università di Pisa, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Balsamo
authors.forename: B
authors.initials: B
authors.lastname: Macchia
authors.forename: E
authors.initials: E
authors.lastname: Orlandini
authors.forename: A
authors.initials: A
authors.lastname: Rossello
authors.forename: F
authors.initials: F
authors.lastname: Macchia
authors.forename: G
authors.initials: G
authors.lastname: Broccali
authors.forename: W
authors.initials: W
authors.lastname: Fonio
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001398:Aztreonam / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D005612:Freeze Drying; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D008826:Microbial Sensitivity Tests; D008997:Monobactams / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
chemical_list: D000900:Anti-Bacterial Agents; D008997:Monobactams; D001398:Aztreonam